How can I have a hard conversation at work? | Handel Group

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7 Simple(ish) Steps To Having A Hard Conversation

Now, more than ever, we all need to be upping our game and not (however understandable) our gamey. We need to be listening better and having the hard, honest, and necessary conversations. Where we used to possibly try and not make waves and “get over ourselves,” all the while still grumbling inside (and/or gossiping outside) when someone told a joke, forwarded a meme, made a comment we didn’t appreciate, or worse, we need to speak our truth with grace and wisdom. Silence, after all, is an accomplice.

So, how can you foster honesty in workplace relationships, let alone in personal ones? 

At Handel Group, we’ve been teaching clients how to have difficult conversations and the art of honesty for over twenty years, from CEOs to executives to parents to students to artists and more. In fact, we have taught it so many times that we’ve recorded the coaching in Module 9 of Inner.U, our online coaching course. 

What we have learned is that every good conversation has a balance of grace and wisdom. The wisdom part is saying the thing you need to communicate: the question or the request. The grace part is the way it’s communicated so that it’s easy to hear. Simple as it sounds, like anything else, it takes practice and, well, more practice. Another reason why we offer lifetime access to Inner.U once you purchase it, you can revisit Module 9 over and over whenever the need for a hard conversation arises.  

Here are the basic steps:

  1. Get permission before having the conversation.

You don’t want to just walk into the office (or, these days, a Zoom call) and launch into a conversation the other person isn’t prepared for, doesn’t have time for, etc. You may say something like, “I want to have a conversation with you about X and Y because I’m really committed to our relationship. Is it okay for us to discuss this now?” If the person says “no” you can then ask, “when would you be available for the conversation?”


  1. Frame the conversation based on your commitment.

I’m not a proponent of honesty for the sake of dumping. There should be a purpose behind the conversation, such as a commitment to your workplace or to the relationship. Explain the context for having the conversation. Usually the commitment is larger than the specific topic of the conversation you are having.


  1. Articulate your concerns about having the conversation.

For example: “I’m afraid to have this conversation because I’m afraid you’ll get mad at me,” or “I’m concerned you’ll think this is none of my business,” or even “I’m afraid I’ll get in trouble.”


  1. Don’t assume your version is true.

You have an opinion and think you know what the facts are. Get their truth about the situation. Ask “what do you think about what I just said?” I remember how a client of mine felt she did not have the position at work she deserved. The client had formed her own reasons why. However, on speaking with her boss, she discovered her assumptions were incorrect. When people avoid making assumptions, situations get resolved faster because there is more openness to hearing others’ perspectives. It also seems things are not taken as personally. We hide things, thinking we are protecting ourselves and others, when we are accomplishing neither. Most of us tell ourselves we are hiding out of kindness to the other person…this is almost never true! And, come on, if you aren’t being your real self how will you ever really feel known for who you are? Answer: You can’t.


  1. Preparation: Write it out, practice with a friend, coach, or both.

Don’t roll your eyes. We have all our clients, co-workers, and friends write out their script first. It’s amazingly helpful and if you want to be sure your tone has the right balance of grace and wisdom, practice it with a friend. One that is committed to the resolution, not your former assumptions getting proven. 

P.S. It won’t just prepare you better, it will deepen your friendship.

Of course, if you need more help, you can always schedule a coaching call to go over your hard conversation before you have it. Schedule a free consultation to learn more about our coaching services and schedule your first session!

We know this is never easy. But, we also know that it’s easy to be great when times are great. It’s times exactly like these where we need, more than ever, to not stay silent and to teach and to listen and to act. People who speak up become leaders. When you become someone who tells the truth about how you feel and what you want, people relate to you differently. If you do it with grace, people will even want to be more honest with you. You will find yourself more powerful as a result of being someone who is willing to have the tough conversations and you will want to do something with it. Please do

Telling the truth to others starts with telling the truth to yourself. Join us for an upcoming Design Your Life, Design Your Quarantine webinar to learn more about having a vision and taking the right actions to become the leader you want to be, both personally and professionally.

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  1. Listen UP (as in, from your higher self).

Listening is also key.

Please know that listening to understand another person’s perspective or experience is NOT the same thing as agreeing with them. This is a very important distinction. This is what we know from working with thousands of people: if you resist someone’s experience they will hold tight to it. If you accept it, they may release it. Listening without adding judgement, reaction, or making it about you is an extremely powerful skill. If you just keep reflecting back what the person has told you and taking it in, the speaker will dig into deeper layers of truth before your very eyes. In the end, you will hear what was really going on, and you will be much more likely to hear ownership on their part. Many of us are more interested in what we want to say next, making our point, being right, and exacting an apology — we miss the opportunity of helping someone come to that mature conclusion themselves.


  1. Resolving, Negotiating, Promises, and Plans

Once two people have shared their experiences or given their perspectives, it will be clear where there is incompatibility or disagreement. In this beat of the conversation, each person can own up to or agree with whatever they can, ask clarifying questions, and offer compromises or resolutions. It’s tempting to wrap up and hope similar situations will never happen again, but it’s important to put in one more beat of wisdom here: promises and plans. Yes, the promise land…for a change. 

Good news, it requires no flights, just actions. 

Obviously, these are important times and an opportunity to find your true voice and be you, only better, louder, more honest, and, yes, graceful. You know how some commercials (back in the day) used to have a warning label at their end: something along the lines of, “don’t do this at home.” THIS is the opposite. Follow the directions, practice, and please do it at work, at home, at, at, at…

TRUE-ly yours,

Gaby Jordan